I am looking for a (pre-owned)Towboat shopping hot spot east of the Mississippi to go shopping this spring. I can drive as far south as Eastern Tennessee, Northern Virginia, in 1 day. Basically I want to be able to look at several boats (at dealers) in a small region. I might have 3-4 days max to shop. I guess I would tow it home. Since It would involve gas, and lodgings that has to be factored into any difference to see if it is worth it.

Where I live (Ontario-Canada) the pickings are slim, and overpriced (I think)

It depends on what brand of boat you're looking for. Some boats have more of a concentration in certain parts of the country usually as a result of a strong dealer presence. For instance, Nautiques are concentrated in the Dallas area because of Buxton Marine.

Onlyinboards is a great starting point. You can also use searchtempest to search craigslist, oodle and ebay. Google it if you don't know what it is. You can set it to search certain areas and save the searches. Searchtempest allows you to search multiple cities at once.

It's going to be hard to find 2-3 dealers that will have multiple used boats on hand to look at that fit your criteria.

I live in Erie PA (not to far from you really) and have purchased 2 boats from florida. one for me and one for my brother-in-law. both times it was well worth the trip. we were not going to try several different boats though. we had found them on craigslist and rolled the dice on making the 16 hour trip one way to get them.
you are correct that boat prices in this area are inflated.

I live in Erie PA (not to far from you really) and have purchased 2 boats from florida. one for me and one for my brother-in-law. both times it was well worth the trip. we were not going to try several different boats though. we had found them on craigslist and rolled the dice on making the 16 hour trip one way to get them.
you are correct that boat prices in this area are inflated.

Florida or Texas is starting to look like the destination, guess I will have to get a map of both study the market and pinpoint geographically where all of the adds are. Here it is Ontario's traditional cottage country of the near north. It is a wealthy mans playground area...and the boats are priced accordingly.

I am curious how much were you able to talk down the owners from their asking price. For me to go that far there would have to be $7 or $8k cheaper than here. Right now there seems to be about a $3 or $4k difference.

The prices are even more inflated once you cross the border into Canada. I live near Winnipeg and my purchases with road-trips have included Atlanta, Albuquerque, State College PA, Dallas, Indianapolis and Minneapolis. As the OP suggested, you have to factor in the road-trip and potentially, a shipping service (my truck from Houston) plus your time. Again, eBay, Only Inboards and other sites can get you a number of leads, but only you can pull the trigger for the purchase. Sometimes you can find a real good deal on a dealer year-end close-out or a distress sale (divorce, etc). Coming up over the next few months there will be some smoking deals if you are patient and able to jump on them when they appear. The southern states and sometimes out west have typically had better prices. Good luck.

I bought my 05' 23' enzo three years ago with around 75 hours on it he was asking $27000. My brother -in-law paid around $27000 for his 05' 23' moomba with around 200 hours on it and that was 4 yrs ago. Both in Florida and in travel and they were both a steel.
I spent about 7 months searching for mine.

1) ask for a TON of pictures. 30+ of ALL areas of the boat
2) Ask for a contact at whatever marina / dealer services the boat. talk to them. Ask about how it was serviced, winterized, thoughts on the seller, etc
3) see if they can send you a compression test